a-lister leonardo dicaprio is very well known for having dated likely the longest list of supermodels in hollywood, but if the rumors are true, the titanic star is a closeted homosexual. In 2013 leo was suspected to have been secretly messing around with his the great gatsby co-star tobey maguire. Actor and producer, tobey maguire is the son of wendy, a secretary turned screenwriter and film producer, and vincent maguire, a construction worker, and cook. He is best known for portraying the main role as peter parker in spiderman series. tobey maguire dated actress sara gilbert for three years from 19 then, he dated actress rashida jones for three and a half years from 1997. Maguire met jennifer meyer, the jewelry designer, in 2003 during his shoot of the movie. Wendy maguire responded to kast, i figured this subject would come up sooner or later. But i think leo and tobey are the crossover between men and women. Like countless other hollywood stars, tobey maguire is most probably gay or at the very least, bisexual. But as hard as it is to come out of the closet for a regular joe - imagine how much more. last may, diners, including host george clooney, salma hayek, tobey maguire and robert downey jnr, paid a reported 40,000 each to attend a special dinner for obama. she met tobey maguire in 2003 while maguire was shooting the movie seabiscuit at universal studios, and became engaged in april 2006. Their daughter ruby sweetheart maguire was born november 10, 2006. Think it might have been one of those oops pregnancies and he insisted on doing the honorable thing by marrying her. leonardo dicaprio and tobey maguire could have easily ended up as hollywood rivals as they were constantly going after the same roles since they.